Last Updated on March 31, 2024

Are you looking for the best cities for winter in Florida? If so, you’ve come to the right place.

With warm days, plenty of outdoor adventures, and none of the bitter cold and snow flurries of the northern states, winter is a fabulous time of year to visit Florida.

Let’s dive into your guide to the 5 of the best Florida cities for a winter escape.



5 Of The Best Cities To Visit For Winter In Florida

white sand beach and coastal hotels in Destin Florida



crowds and people in the docks of Destin Bay in Florida

Crowds In Destin In Winter

The winter season in North Florida is pretty chill, with few crowds, especially compared to the typically packed beaches and water parks of summer.

The exception is during the Christmas holidays when families go on vacation.

What To Wear In Destin During The Winter Months

Although Destin has mild winters, you should be prepared for cool nights and cold snaps.

The weather can vary dramatically day by day–dropping from 30 one day and rising to 70 the next.

With this in mind, one of the best things to do is wear layers.

Start with something you’d feel comfortable wearing in warm temperatures, then add a warm layer or two for cold weather.

Festivals In Destin In The Winter

  • Sandestin Gumbo Festival
  • Holiday on the Harbor Festival

  • Baytowne on Ice

  • Winter Concert Series

  • Harbor Boat Parade

Check out this fun tour from Destin 👉 Private Chartered Pontoon Boat 🛥️



panoramic view of Clearwater Beach Florida



crowds and people silhouettes during a beautiful sunset in Clearwater Beach Fl

Photo credit – Unsplash by Abhishek Rao

Crowds In Clearwater Beach In Winter

Clearwater Beach is a relatively compact island, so it can get pretty crowded. The fact that it’s a year-round tourist destination doesn’t help.

However, there tend to be far fewer crowds on the beaches in January and February.

What To Wear In Clearwater Beach During The Winter Months

I recommend taking summer clothes to Clearwater Beach but round out your wardrobe with light jackets, light pants, and closed-toed shoes for the cooler temperatures at night.

Festivals In Clearwater Beach In The Winter

  • Enchant in St. Pete’s

  • Shopapalooza Festival

  • Clearwater Yacht Club Annual Holiday Boat Parade

  • Nutcracker Magical Christmas Ballet

Check out this amazing boat tour from Clearwater Beach 👉 Half-Day Private Boating On Tahoe Funship 🛥️



beautiful Naples Florida skyline at dawn



Naples Florida beach scene at winter

Crowds In Naples In Winter

Naples can get busy in the winter because it has gained fame for its amazing climate.

In fact, this is the peak season for Naples.

What To Wear In Naples During The Winter Months

Naples, Florida’s weather is typically sunny and warm, with average temperatures of 68º in January.

Be sure to pack a mixture of summer-style clothes and Fall-weather jackets and sweaters for evenings and cold snaps.

Festivals In Naples In The Winter

  • Naples Boat Show

  • Winter Wine Festival

  • Cars on Fifth

  • The Chubb Classic

  • Annual Naples National Art Festival

Book the best Dolphin Tour in Naples 👉 Naples Sightseeing Boat Tour 🐬



aerial view of the beach and buildings in Sarasota Beach FL



aerial view of Lido Beach in Sarasota Florida

Crowds In Sarasota In Winter

Sarasota can be quite crowded during the winter due to the influx of older adults fleeing snowy weather conditions in their hometowns.

January through March is the peak season.

What To Wear In Sarasota During The Winter Months

Start with a tank top, then add a sweater, a light jacket, and a scarf—this way, you’ll be prepared for any range of temperature from sunny and warm to deliciously chilly.

Festivals In Sarasota In The Winter

  • Sarasota Country Music Festival

  • Siesta Beach Seafood & Music Festival

  • Sarasota Christmas Glow Run 5k

  • New Year’s Eve Block Party and Pineapple Drop



Explore Sarasota’s Mangroves with this tour 👉 Kayak Tour Through Mangrove Tunnels 🐬



beach stores in Panama City Beach Florida



view from the ocean of Panama City beach with people swimming

Crowds In Panama City Beach In Winter

Unlike some Central and South Florida destinations, Panama City Beach tends to be blissfully quiet in the winter.

What To Wear In Panama City Beach During The Winter Months

Panama City Beach tends to be windy, so be sure to pack a light windbreaker and some warm layers.

You may also want a rain poncho, but leave your umbrella at home so it doesn’t get turned inside out in the gusts.

Festivals In Panama City Beach In The Winter

  • Food Truck Festival

  • Mardi Gras and Music Festival

  • Panama City Beach Scottish Festival

👉 Book this Shell Tour from Panama City Beach! Shell Island Snorkel Snorkel And Dolphin Catamaran Cruise 🐬



panoramic view of the city buildings and pal trees in a city in Florida

How Cold Is It In Florida In The Winter?

Florida’s winters are quite mild, but the temperature range between Northern and Southern Florida can be very different.

Key West and Miami Beach are among the warmest, while places like Daytona Beach will be colder.

What Is The Coldest Month In Florida?

January is the coldest month in Florida, with average high temperatures ranging between the 60s and 70s and lows ranging from the 40s to the mid-sixties.

Temperatures tend to fluctuate, so you could have short weather one day and want to wear a sweater and scarf on another.

How Long Does Winter Last In Florida?

Winter in Florida lasts from two to three months, roughly from December until February.

Does Florida Have 4 Seasons?

Yes–Florida has all four seasons. Winter temperatures can drop below freezing in northern Florida, with rare snow snowstorms happening some years.



Final Thoughts: 5 Best Cities For Winter In Florida

And there you have it, 5 Of The Best Cities For Winter In Florida. Which one will you add to your vacation plans?

For the full list of Vacasa’s best cities for winter in Florida, check out this post. 



Always On The Shore contains affiliate links and if you make a purchase, we make a small commission at no cost to you.

For more information, please read the disclaimer page


Booking a last-minute trip to Florida?  

If so, we have you covered.  

Top Tours in Florida – Viator

Top Rated Hotels & Accommodations –

Looking To Get Around In Florida

Check out rental car rates here! 🚗